# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_665_ak_nm-288
_database_code_depnum_ccdc_archive 'CCDC 2159571'
loop_
_audit_author_name
_audit_author_address
'Krishnan Rangan'
;Birla Institute of Technology and Science Pilani Hyderabad Campus
India
;
_audit_update_record             
;
2022-03-17 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;
_audit_creation_date             2020-08-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 N2 O S'
_chemical_formula_sum            'C19 H14 N2 O S'
_chemical_formula_weight         318.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H13 N2 O S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6918(2)
_cell_length_b                   7.7847(2)
_cell_length_c                   13.7184(3)
_cell_angle_alpha                90.026(2)
_cell_angle_beta                 97.054(2)
_cell_angle_gamma                114.557(3)
_cell_volume                     740.27(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5498
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      79.6750
_cell_measurement_theta_min      6.2490
_shelx_estimated_absorpt_T_max   0.907
_shelx_estimated_absorpt_T_min   0.826
_exptl_absorpt_coefficient_mu    1.982
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7457
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.208
_diffrn_reflns_theta_min         6.261
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00  32.00   0.50    1.34    --    0.00  19.00   0.00  108
  2  ω    -36.00  14.00   0.50    1.34    --    0.00 -37.00   0.00  100
  3  ω     29.00  86.00   0.50    1.34    --    0.00  77.00 120.00  114
  4  ω     55.00  89.00   0.50    1.34    --    0.00  19.00   0.00   68
  5  ω    -28.00  10.00   0.50    1.34    --    0.00  77.00 120.00   76
  6  ω    -82.00 -56.00   0.50    1.34    --    0.00 -37.00   0.00   52
  7  ω     95.00 126.00   0.50    5.40    --  107.20 -45.00  90.00   62
  8  ω     89.00 126.00   0.50    5.40    --  107.20  30.00 -90.00   74
  9  ω    154.00 197.00   0.50    5.40    --  107.20  15.00-150.00   86
 10  ω     35.00 138.00   0.50    5.40    --  107.20 -82.00   0.00  206
 11  ω    147.00 173.00   0.50    5.40    --  107.20  30.00 -60.00   52
 12  ω    130.00 158.00   0.50    5.40    --  107.20  30.00 -90.00   56
 13  ω    163.00 195.00   0.50    5.40    --  107.20  30.00 -90.00   64
 14  ω     19.00 139.00   0.50    5.40    --  107.20 -82.00-150.00  240
 15  ω     86.00 127.00   0.50    5.40    --  107.20 -82.00 120.00   82
 16  ω     80.00 194.00   0.50    5.40    --  107.20  15.00   0.00  228
 17  ω     75.00 110.00   0.50    5.40    --  107.20 -61.00 -30.00   70
 18  ω     39.00  65.00   0.50    5.40    --  107.20 -61.00 -30.00   52
 19  ω     18.00  86.00   0.50    5.40    --  107.20 -30.00   0.00  136
 20  ω     65.00 129.00   0.50    5.40    --  107.20 -82.00 -90.00  128
 21  ω     18.00 128.00   0.50    5.40    --  107.20 -61.00  90.00  220
 22  ω     99.00 126.00   0.50    5.40    --  107.20  30.00 -60.00   54
 23  ω     85.00 130.00   0.50    5.40    --  107.20  15.00-150.00   90
 24  ω     93.00 118.00   0.50    5.40    --  107.20 -82.00  60.00   50
 25  ω     63.00 106.00   0.50    5.40    --  107.20 -82.00  90.00   86
 26  ω     23.00  95.00   0.50    5.40    --  107.20 -45.00-120.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0301338000
_diffrn_orient_matrix_UB_12      0.0638969000
_diffrn_orient_matrix_UB_13      0.1094440000
_diffrn_orient_matrix_UB_21      0.0822800000
_diffrn_orient_matrix_UB_22      -0.1459526000
_diffrn_orient_matrix_UB_23      0.0275096000
_diffrn_orient_matrix_UB_31      0.2042439000
_diffrn_orient_matrix_UB_32      0.1486892000
_diffrn_orient_matrix_UB_33      -0.0105507000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2876
_reflns_number_total             3095
_reflns_odcompleteness_completeness 99.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3095
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0891P)²+0.2026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1397
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C17A-C16
 1.4 with sigma of 0.02
 C18-C17A
 1.49 with sigma of 0.02
3. Others
 Fixed Sof: S1A(0.7) C17A(0.7) H17A(0.7) H19(0.7) H19A(0.3) H18(0.7) H18A(0.3)
 S1B(0.3) C17B(0.3) H17B(0.3)
4.a Aromatic/amide H refined with riding coordinates:
 C17A(H17A), C11(H11), C12(H12), C3(H3), C13(H13), C7(H7), C14(H14), C4(H4),
 C15(H15), C19(H19), C19(H19A), C18(H18), C18(H18A), C17B(H17B)
4.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.05917(16) -0.28542(13) 0.42193(7) 0.0215(2) Uani 0.7 1 d . . P A 1
C17A C 0.1496(9) 0.0482(7) 0.3666(4) 0.0238(10) Uani 0.7 1 d D . P A 1
H17A H 0.207330 0.182075 0.364300 0.029 Uiso 0.7 1 calc R . P A 1
O3 O 0.43360(16) 0.16988(16) 0.89499(8) 0.0243(3) Uani 1 1 d . . . . .
N1 N 0.44436(17) 0.00614(17) 0.70717(9) 0.0149(3) Uani 1 1 d . . . . .
N2 N 0.4041(2) -0.29292(18) 0.70569(10) 0.0216(3) Uani 1 1 d . . . . .
C1 C 0.3432(2) -0.0780(2) 0.61388(10) 0.0164(3) Uani 1 1 d . . . . .
C11 C 0.7356(2) 0.5177(2) 0.96772(11) 0.0185(3) Uani 1 1 d . . . . .
H11 H 0.641353 0.454745 1.009576 0.022 Uiso 1 1 calc R . . . .
C2 C 0.3030(2) 0.0383(2) 0.54158(10) 0.0158(3) Uani 1 1 d . . . . .
C9 C 0.5430(2) 0.2639(2) 0.83809(10) 0.0172(3) Uani 1 1 d . . . . .
C12 C 0.8952(2) 0.6826(2) 1.00206(11) 0.0226(3) Uani 1 1 d . . . . .
H12 H 0.909216 0.733281 1.067038 0.027 Uiso 1 1 calc R . . . .
C3 C 0.3758(2) 0.2289(2) 0.56488(11) 0.0183(3) Uani 1 1 d . . . . .
H3 H 0.360575 0.310209 0.516236 0.022 Uiso 1 1 calc R . . . .
C10 C 0.7129(2) 0.4438(2) 0.87153(10) 0.0161(3) Uani 1 1 d . . . . .
C5 C 0.5010(2) 0.1977(2) 0.73209(10) 0.0160(3) Uani 1 1 d . . . . .
C13 C 1.0350(2) 0.7740(2) 0.94140(12) 0.0237(3) Uani 1 1 d . . . . .
H13 H 1.143767 0.887371 0.964832 0.028 Uiso 1 1 calc R . . . .
C7 C 0.3204(2) -0.2626(2) 0.61765(11) 0.0197(3) Uani 1 1 d . . . . .
H7 H 0.255026 -0.356752 0.565738 0.024 Uiso 1 1 calc R . . . .
C6 C 0.4791(2) -0.1308(2) 0.75879(11) 0.0176(3) Uani 1 1 d . . . . .
C14 C 1.0153(2) 0.6993(2) 0.84662(11) 0.0218(3) Uani 1 1 d . . . . .
H14 H 1.112061 0.760691 0.805789 0.026 Uiso 1 1 calc R . . . .
C4 C 0.4738(2) 0.3078(2) 0.66020(10) 0.0173(3) Uani 1 1 d . . . . .
H4 H 0.521089 0.440329 0.673907 0.021 Uiso 1 1 calc R . . . .
C15 C 0.8550(2) 0.5354(2) 0.81125(11) 0.0191(3) Uani 1 1 d . . . . .
H15 H 0.841689 0.485467 0.746194 0.023 Uiso 1 1 calc R . . . .
C16 C 0.1859(2) -0.0439(2) 0.44664(11) 0.0168(3) Uani 1 1 d D . . . .
C8 C 0.5959(2) -0.0994(2) 0.85706(11) 0.0227(3) Uani 1 1 d . . . . .
H8A H 0.706729 0.024019 0.861251 0.034 Uiso 1 1 calc GR . . . .
H8B H 0.641701 -0.199169 0.866594 0.034 Uiso 1 1 calc GR . . . .
H8C H 0.516382 -0.102369 0.908189 0.034 Uiso 1 1 calc GR . . . .
C19 C -0.0336(2) -0.2561(2) 0.31071(12) 0.0242(3) Uani 1 1 d . . . . .
H19 H -0.116876 -0.360525 0.267058 0.029 Uiso 0.7 1 calc R . P A 1
H19A H -0.118596 -0.371925 0.275825 0.029 Uiso 0.3 1 calc R . P A 2
C18 C 0.0157(2) -0.0758(2) 0.28571(12) 0.0243(4) Uani 1 1 d D . . . .
H18 H -0.029151 -0.036790 0.225884 0.029 Uiso 0.7 1 calc R . P A 1
H18A H -0.030003 -0.054314 0.221408 0.029 Uiso 0.3 1 calc R . P A 2
S1B S 0.1491(5) 0.1060(4) 0.3601(2) 0.0208(5) Uani 0.3 1 d . . P A 2
C17B C 0.0873(19) -0.2187(17) 0.4113(9) 0.039(3) Uani 0.3 1 d . . P A 2
H17B H 0.091190 -0.320837 0.448041 0.047 Uiso 0.3 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1A C16 1.7309(18) . ?
S1A C19 1.6607(19) . ?
C17A C16 1.374(5) . ?
C17A C18 1.455(6) . ?
O3 C9 1.2258(19) . ?
N1 C1 1.4155(17) . ?
N1 C5 1.3973(18) . ?
N1 C6 1.3786(18) . ?
N2 C7 1.3653(19) . ?
N2 C6 1.322(2) . ?
C1 C2 1.435(2) . ?
C1 C7 1.375(2) . ?
C11 C12 1.387(2) . ?
C11 C10 1.401(2) . ?
C2 C3 1.372(2) . ?
C2 C16 1.4661(19) . ?
C9 C10 1.487(2) . ?
C9 C5 1.4934(19) . ?
C12 C13 1.392(2) . ?
C3 C4 1.424(2) . ?
C10 C15 1.401(2) . ?
C5 C4 1.361(2) . ?
C13 C14 1.389(2) . ?
C6 C8 1.485(2) . ?
C14 C15 1.389(2) . ?
C16 S1B 1.745(3) . ?
C16 C17B 1.309(13) . ?
C19 C18 1.349(2) . ?
C19 C17B 1.521(13) . ?
C18 S1B 1.622(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 S1A C16 92.08(9) . . ?
C16 C17A C18 114.6(3) . . ?
C5 N1 C1 122.09(12) . . ?
C6 N1 C1 107.24(12) . . ?
C6 N1 C5 130.57(12) . . ?
C6 N2 C7 107.03(13) . . ?
N1 C1 C2 118.92(13) . . ?
C7 C1 N1 104.15(12) . . ?
C7 C1 C2 136.77(13) . . ?
C12 C11 C10 120.21(14) . . ?
C1 C2 C16 121.17(13) . . ?
C3 C2 C1 117.69(13) . . ?
C3 C2 C16 121.14(13) . . ?
O3 C9 C10 121.69(13) . . ?
O3 C9 C5 118.90(13) . . ?
C10 C9 C5 119.40(13) . . ?
C11 C12 C13 120.07(14) . . ?
C2 C3 C4 121.60(14) . . ?
C11 C10 C9 118.78(13) . . ?
C15 C10 C11 119.39(14) . . ?
C15 C10 C9 121.76(13) . . ?
N1 C5 C9 119.27(12) . . ?
C4 C5 N1 117.80(13) . . ?
C4 C5 C9 121.23(13) . . ?
C14 C13 C12 120.01(15) . . ?
N2 C7 C1 111.19(13) . . ?
N1 C6 C8 125.32(13) . . ?
N2 C6 N1 110.37(13) . . ?
N2 C6 C8 124.18(14) . . ?
C13 C14 C15 120.31(15) . . ?
C5 C4 C3 121.44(14) . . ?
C14 C15 C10 119.99(14) . . ?
C17A C16 S1A 109.0(2) . . ?
C17A C16 C2 128.4(3) . . ?
C2 C16 S1A 122.54(12) . . ?
C2 C16 S1B 119.01(14) . . ?
C17B C16 C2 132.5(5) . . ?
C17B C16 S1B 108.3(6) . . ?
C18 C19 S1A 116.38(13) . . ?
C18 C19 C17B 99.2(5) . . ?
C19 C18 C17A 107.9(2) . . ?
C19 C18 S1B 123.22(16) . . ?
C18 S1B C16 89.92(14) . . ?
C16 C17B C19 119.0(8) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.172
_oxdiff_exptl_absorpt_empirical_full_min 0.617
